1-Bromo-2,2,2-trifluoroethyl difluoromethyl ether

ABSTRACT

The novel compound 1-bromo-2,2,2-trifluoroethyl difluoromethyl ether having the formula CF3CHBr-O-CHF2 is prepared through bromination of 2,2,2-trifluoroethyl difluoromethyl ether. The brominated compound is useful as an inhalation anesthetic and as a solvent and dispersant for fluorinated materials.

United States Patent [1 1 Terrell Sept. 9, 1975 l-BROMO-2,2,2-TRIFLUOROETHYL DIFLUOROMETHYL ETHER [75] Inventor: Ross C. Terrell, Plainfield, NJ.

[73] Assignee: Airco, Inc., Montvale, NJ,

[22] Filed: May 7, 1973 [21] Appl. No.: 358,209

Related US. Application Data [62] Division of Ser. No. 139,862, May 3, 1971, Pat. No.

FOREIGN PATENTS OR APPLICATIONS 8/1969 Germany 260/614 F OTHER PUBLICATIONS Croix et al., CA. 72, (1970), 3004b.

Larsen, Fluorine Chemistry Reviews, Vol. 3 (1969), 38-39.

Primary ExaminerHoward T. Mars Attorney, Agent, or Firm-Roger M. Rathbun; Edmund W. Bopp; l-l. Hume Mathews [5 7] ABSTRACT The novel compound 1-bromo-2,2,2-trif1uoroethyl difluoromethyl ether having the formula CF CHBr-O--CHF is prepared through bromination of 2,2,2-trifluoroethyl difluoromethyl ether. The brominated compound is useful as an inhalation anesthetic and as a solvent and dispersant for fluorinated materials.

1 Claim, N0 lDrawings 1-BROM0-2,2,2-'I'RIFLUOROET DIFLUOROTHYL ETHER This is a division of application Ser. No. 139,862,

2 distillation and preparative gas chromatography, bp. 64.5C., N 1.3297.

Calculated Formulation C3H2BI'F5O C,15.7: H, 0.87; Found: C,l6.0; H, 0.89

filed May 3,1971, now Pat. No. 3,764,705, issued Oct. 5 The desired compound was further identified by infra- 9, 1973. red spectra.

This invention relates to the compound l-bromo- In order to determine the potency of l-bromo-2,2,2- 2,2,2-trifluoroethyl difluoromethyl ether and its use in trifluoroethyl difluoromethyl ether as an inhalation anproducing anesthesia in anesthetic-susceptible, airesthetic in combination with oxygen, tests were carried breathing mammals. out on mice. The l-bromo-2,2,Z-trifluoroethyl di- The compound l-bromo-2,2,2-trifluorethyl difluoromethyl ether used was at. least 99.5% pure as defluoromethyl ether has the following formula: termined by vapor phase chromatography.

In the tests, groups of five mice were placed into a jar CF3CHBI'TO CHF2 and exposed to a concentration of 0.5 to 2.5% by vol- This ether is normally a clear, colorless liquid with a ume of 1-bromo-2,2,2-trifluoroethyl difluoromethyl not unpleasant odor, and has the following physical ether. After an induction time which was free of excitaproperties: boiling point 645C; vapor pressure 175 tion, the mice were anesthetized and then recovered. mm. at C.; specific gravity 1.9; refractive index N The results of these pharmacologic tests were as foll.3297 and molecular weight 229. The compound is lows:

No, of Animals Inhal, Induc. Recovery Tested Conc. Time Time Remarks 5 0,571 4m.*4()s.** lm.40s. to pain Smooth induction 26s. to walking Very light anesthesia. Rapid. complete recovery. 10 [.092 58s. 57s. to pain Uneventful.

lm.40s, to walk 10 1.57: 275. lm.52s. to pain Quick smooth in- 3m.6s. to walk -duction. Resp.

depression to rate 32 in maint. Complete recovery fast. 5 2.571 20s. 7m.3 Is. to pain Ditto.

7m.29s. to walk m minutes *s seconds Tail cli test a reaction to pain created by a tail clip nonflammable, soda lime stable, and a potent anesthetic for anesthetic-susceptible mammals. This ether is also easily miscible with other organic liquids including fats and oils and has useful solvent properties, for example, as a solvent for fluorinated olefins and other fluorinated materials such as fluoro waxes. The com pound may be used to prepare pastes and dispersions of such materials useful for coatings and the like and may be used as a degreasing agent.

The compound l-bromo-2,2,2-trifluoroethy1 difluoromethyl ether can be prepared by brominating 2,2,2-trifluoroethyl difluoromethyl ether, i.e. CF CI-I OCHF whose preparation is described in US. Pat. No. 3,535,425. The bromination can be carried out at temperatures of about 425 to 500C, and best results are usually found at about 450 to 475C. Following the bromination the reaction mass can be separated by fractional distillation or by vapor phase chromatography.

The following example will illustrate the preparation of l-bromo2,2,2trifluoroethyl difluoromethyl ether. The feed ether, CF CH -O-CHF (76 g), was charged to a bubbler. Nitrogen at 5-10 liters per hour, was passed through the bubbler and into another bubbler containing bromine. The resulting ether and brominecontaining gas stream was then passed through a l X 12 glass tube maintained at 450C. by an electrical heater. The product was collected in a trap at 78C. After six hours, 73 grams of CF CH and 41 g. of bromine had been reacted. The product was recovered by These tests show that l-bromo-2,2,2-trifluoroethyl difluoromethyl ether is a potent anesthesia agent which is rapidly taken up and excreted by warm-blooded mammals. This anesthetic produced muscle flaccidity during maintenance, and, in high concentrations caused marked respiratory depression which did not persist into the recovery period. The anesthetized animals recovered rapidly and appeared fully alert. In comparison with the 1-chloro-2,2,2-trifluoroethyl difluoromethyl ether anesthetic agent of my US. Pat. No. 3,535,425 the anesthesia of the present invention gives comparable induction times in lesser concentrations. Thus with mice, 2.5% of the agent of my prior patent gave an induction time of 30 seconds which was accomplished with only 1.5% of the anesthesia of this invention.

The anesthetic agent of the invention may be administered by any of the well known techniques used for the administration of general inhalation agents, such as the open drop, semiclosed, and closed systems. The agent may also be administered as an injectable anesthetic as taught by John C. Krantz, Jr. in U.S. Pat. No. 3,216,897 issued November 9, 1965, and assigned to the assignee of the instant application.

The compound l-bromo-2,2,2-trifluoroethyl difluoromethyl ether exhibits excellent anesthetic properties. The compound is non-flammable and soda lime stable. It lends itself to effective use as an inhalent anesthetic in respirable mixtures containing life-supporting concentrations of oxygen as well as mixtures containing oxygen and other inhalation anesthetics such as nitrous 3 oxide. The effective amount of CF CHBrOCHF- to be employed depends on the level of anesthesia to which the mammal is to be brought, the rate at which anesthesia is to be induced, and the length of time over which anesthesia is to be maintained. Volume percentages of CF -,CHBrOCl-IF in oxygen from a fraction of a percent, e.g. 0.1 to 0.25%, up to several percent, e.g. about can be employed. The amount of anesthesia to be used can be easily regulated, starting with a small amount of the ether and gradually increasing the amount until the desired plane of anesthesia is reached. By then monitoring the physical reactions of 4 the mammal, as is the usual procedure, the duration and plane of anesthesia can be readily controlled.

While there has been described what are at present considered to be the preferred embodiments of the invention, it will be understood that various modifications may be made therein which are within the true spirit and scope of the invention.

I claim:

1. The compound l-bromo-2,2,Z-trifluoroethyl difluoromethyl ether of the formula CF CHBr-OCHF 

1. THE COMPOUND 1-BROMO-2,2,2-TRIFLUOROETHYL DIFLUOROMETHYL ETHER OF THE FORMULA CF3CHBR-0-CHF2. 